Total syntheses of [Beta]-lactone containing natural products : I. total synthesis of belactosin C II. synthetic studies toward spongiolactone /

Bibliographic Details
Main Author: Cho, Sung Wook
Other Authors: Gabbai, Francois P. (Thesis advisor), Romo, Daniel (Thesis advisor)
Format: Thesis eBook
Language:English
Published: [College Station, Tex.] : [Texas A&M University], [2010]
Subjects:
Online Access:Link to OAK Trust copy

MARC

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099 |a 2008  |a Dissertation  |a 1969.1/ETD-TAMU-3121 
100 1 |a Cho, Sung Wook. 
245 1 0 |a Total syntheses of [Beta]-lactone containing natural products :  |b I. total synthesis of belactosin C II. synthetic studies toward spongiolactone /  |c by Sung Wook Cho. 
264 1 |a [College Station, Tex.] :  |b [Texas A&M University],  |c [2010] 
300 |a 1 online resource. 
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500 |a "Major Subject: Chemistry" 
500 |a Title from author supplied metadata (automated record created 2010-03-12 12:08:51). 
502 |b Doctor of Philosophy  |c Texas A&M University  |d 2008  |o http://hdl.handle.net/1969.1/ETD-TAMU-3121 
504 |a Includes bibliographical references. 
516 |a Text (Dissertation) 
520 3 |a The recently isolated bacterial metabolites, belactosins A-C from a fermentation broth of Streptomyces sp. UCK14, uniquely contain a B-lactone dipeptide motif and exhibit anticancer activities. The enantioselective synthesis of (-)-belactosin C and derivatives was accomplished in a concise manner employing the tandem, Mukaiyama aldol-lactonizaton (TMAL) process and test their bioactivities. . One approach involved a distal double diastereoselective TMAL reaction with a dipeptide glyoxamide, whereas a second approach involved amide coupling of a dipeptide with a B-lactone carboxylic acid, obtained via the TMAL process employing a chiral silyl ketene acetal. Enzymatic assays showed that the belactosins act as the dual inhibitors of the proteasome and the thioesterase domain of fatty acid synthase. Spongiolactone which uniquely contains a cyclopentyl-fused B-lactone was isolated in 1986 from Spongi-onellagracilis No biological activity have been reported for this compound; however, the acylating potential of the resident B-lactone warrants screening for potential activity. After many setbacks in the synthesis of spongiolactone, significant progress has been made. Importantly, NCAL process also enabled a concise construction of [3.2.0]-bicyclo B-lactone, which is the key structure in the spongiolactone synthesis and only a few steps remained to complete the synthesis. 
500 |a Electronic resource. 
650 4 |a Major chemistry. 
653 |a TMAL 
653 |a NCAL 
653 |a Synthesis 
653 |a &#946 
653 |a -Lactone 
653 |a Spongiolactone 
653 |a Belactosin C 
700 1 |a Gabbai, Francois P.,  |e thesis advisor. 
700 1 |a Romo, Daniel,  |e thesis advisor. 
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952 f f |a Texas A&M University  |b College Station  |c Electronic Resources  |s www_evans  |d Available Online  |t 0  |e 2008 Dissertation 1969.1/ETD-TAMU-3121  |h Other scheme 
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